| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (0) Peabody/Lynnfield/North Reading Tanners at (1) Masconomet Chieftains | Haverhill Valley Forum |
| December 18, 2019 | (2) Masconomet Chieftains at (1) Beverly/Danvers/Ipswich Panthers | Raymond J. Bourque Arena |
| December 23, 2019 | (5) Masconomet Chieftains at (2) Dover-Sherborn/Hopkinton Raiders | Blackstone Valley Ice Arena |
| December 28, 2019 | (4) Winthrop Vikings at (2) Masconomet Chieftains | Haverhill Valley Forum |
| January 02, 2020 | (3) Masconomet Chieftains at (1) BLUE HAWKS - EXETER NH | The Rinks at Exeter |
| January 04, 2020 | (3) Masconomet Chieftains at (0) Marblehead Magicians | O'Keefe Athletic Center Salem State |
| January 08, 2020 | (0) Masconomet Chieftains at (3) Tewksbury/Methuen Red Rangers | Methuen High School Rink |
| January 11, 2020 | (1) Dover-Sherborn/Hopkinton Raiders at (1) Masconomet Chieftains | Haverhill Valley Forum |
| January 15, 2020 | (0) Masconomet Chieftains at (3) Andover Golden Warriors | Breakaway Ice Center |
| January 18, 2020 | (0) Matignon Warriors at (1) Masconomet Chieftains | Haverhill Valley Forum |
| January 20, 2020 | (2) Masconomet Chieftains at (2) Peabody/Lynnfield/North Reading Tanners | McVann-O'Keefe Skating Rink |
| January 25, 2020 | (2) Masconomet Chieftains at (2) Shrewsbury Colonials | NorthStar Ice Sports |
| February 01, 2020 | (3) Beverly/Danvers/Ipswich Panthers at (5) Masconomet Chieftains | Haverhill Valley Forum |
| February 05, 2020 | (0) Masconomet Chieftains at (1) Winthrop Vikings | Larsen Rink |
| February 08, 2020 | (1) Medford/Malden Mustangs at (6) Masconomet Chieftains | Haverhill Valley Forum |
| February 13, 2020 | (0) Marblehead Magicians at (2) Masconomet Chieftains | Haverhill Valley Forum |
| February 15, 2020 | (0) Masconomet Chieftains at (7) HPNA Hillies | Veterans Memorial Ice Rink |
| February 17, 2020 | (5) Wellesley Raiders at (1) Masconomet Chieftains
NEWBuryport Bank Ice Hockey Classic |
Graf Rink |
| February 19, 2020 | (1) Masconomet Chieftains at (1) Tewksbury/Methuen Red Rangers
NEWburyport BANK Tournament |
Graf Rink |
| February 25, 2020 | (2) Duxbury Dragons at (0) Masconomet Chieftains
Girls D1 Playoff |
Veterans Memorial Ice Rink |
